Harry attended Skerries Community College and is currently studying Retail Management at Dublin Institute of Technology.
Dawson was part of the Dublin U-21 panel which were knocked out of the 2011 All-Ireland Under 21 Football Championship at the first round stage.
Dawson has been part of the DIT Senior Football team for their 2011, 2012 and 2013 O'Byrne Cup Campaigns.
Dawson is an integral member of the Skerries Harps GAA Senior Football team.
In this game Dawson scored a last minute free to give Skerries a 1–11 to 1–10 win.